NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	232.18
Volume:	274.98
LogP:	5.371
LogD:	4.531
LogS:	-4.404
# Rotatable Bonds:	8
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.501
Synthetic Accessibility Score:	1.975
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.688
MDCK Permeability:	1.4900524547556415e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.971
30% Bioavailability (F30%):	0.956

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.162
Plasma Protein Binding (PPB):	99.2079849243164%
Volume Distribution (VD):	1.941
Pgp-substrate:	0.6146840453147888%

ADMET: Metabolism

CYP1A2-inhibitor:	0.95
CYP1A2-substrate:	0.341
CYP2C19-inhibitor:	0.872
CYP2C19-substrate:	0.113
CYP2C9-inhibitor:	0.643
CYP2C9-substrate:	0.974
CYP2D6-inhibitor:	0.924
CYP2D6-substrate:	0.863
CYP3A4-inhibitor:	0.494
CYP3A4-substrate:	0.179

ADMET: Excretion

Clearance (CL):	3.995
Half-life (T1/2):	0.791

ADMET: Toxicity

hERG Blockers:	0.117
Human Hepatotoxicity (H-HT):	0.035
Drug-inuced Liver Injury (DILI):	0.025
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.051
Maximum Recommended Daily Dose:	0.258
Skin Sensitization:	0.948
Carcinogencity:	0.054
Eye Corrosion:	0.972
Eye Irritation:	0.985
Respiratory Toxicity:	0.245

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC280347

Natural Product ID:	NPC280347
*Common Name:**	Gibbilimbol B
IUPAC Name:	4-[(E)-dec-3-enyl]phenol
Synonyms:	4-[(3'E)-Decenyl]Phenol
Standard InCHIKey:	RQVUFITWWLNDGP-BQYQJAHWSA-N
Standard InCHI:	InChI=1S/C16H24O/c1-2-3-4-5-6-7-8-9-10-15-11-13-16(17)14-12-15/h7-8,11-14,17H,2-6,9-10H2,1H3/b8-7+
SMILES:	CCCCCC/C=C/CCc1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL443175
PubChem CID:	10014185
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0004646] 1-hydroxy-2-unsubstituted benzenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO27498	Piper gibbilimbum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9677279]
NPO27498	Piper gibbilimbum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	1
IC50	3
LD50	1
MIC	2
Others	6

Activity Type	# Activity
Cell Line	1
Organism	8
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	3.9	ug ml-1	PMID[555898]
NPT176	Organism	Artemia salina	Artemia salina	LD50	=	4.9	ug ml-1	PMID[555898]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	4.0	ug.mL-1	PMID[555898]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	2.0	ug.mL-1	PMID[555898]
NPT314	Organism	Bacillus cereus	Bacillus cereus	IZ	<	2.0	mm	PMID[555898]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	IZ	<	2.0	mm	PMID[555898]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	75300.0	nM	PMID[555899]
NPT27	Others	Unspecified		CC50	=	254100.0	nM	PMID[555899]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	3.4	n.a.	PMID[555899]
NPT1219	Organism	Leishmania chagasi	Leishmania chagasi	IC50	=	100400.0	nM	PMID[555899]
NPT1219	Organism	Leishmania chagasi	Leishmania chagasi	IC50	=	94900.0	nM	PMID[555899]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	2.5	n.a.	PMID[555899]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	2.7	n.a.	PMID[555899]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC280347 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	232
0.1-0.2	2038
0.2-0.3	6818
0.3-0.4	12470
0.4-0.5	6781
0.5-0.6	9155
0.6-0.7	3962
0.7-0.8	912
0.8-0.85	202
0.85-0.9	80
0.9-0.95	32
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC177420
0.9882	High Similarity	NPC55561
0.9881	High Similarity	NPC25493
0.9881	High Similarity	NPC113460
0.9765	High Similarity	NPC242240
0.9765	High Similarity	NPC318325
0.9765	High Similarity	NPC123273
0.9762	High Similarity	NPC23167
0.9643	High Similarity	NPC197783
0.9535	High Similarity	NPC258219
0.9535	High Similarity	NPC98772
0.9529	High Similarity	NPC184169
0.9524	High Similarity	NPC248817
0.9524	High Similarity	NPC175313
0.9438	High Similarity	NPC26244
0.9405	High Similarity	NPC265146
0.9405	High Similarity	NPC124436
0.9333	High Similarity	NPC473388
0.9326	High Similarity	NPC27323
0.9326	High Similarity	NPC151715
0.9326	High Similarity	NPC316301
0.9318	High Similarity	NPC304541
0.9318	High Similarity	NPC270547
0.9302	High Similarity	NPC407
0.9302	High Similarity	NPC307235
0.9213	High Similarity	NPC210497
0.9213	High Similarity	NPC3358
0.9213	High Similarity	NPC138117
0.9213	High Similarity	NPC325292
0.9213	High Similarity	NPC306884
0.9213	High Similarity	NPC162314
0.9213	High Similarity	NPC147284
0.9213	High Similarity	NPC94139
0.9205	High Similarity	NPC300017
0.9205	High Similarity	NPC192
0.9195	High Similarity	NPC27974
0.9186	High Similarity	NPC155393
0.9101	High Similarity	NPC155908
0.9101	High Similarity	NPC45040
0.9101	High Similarity	NPC204210
0.907	High Similarity	NPC286904
0.9032	High Similarity	NPC225506
0.9022	High Similarity	NPC225464
0.9022	High Similarity	NPC77492
0.9011	High Similarity	NPC313650
0.9011	High Similarity	NPC8392
0.8977	High Similarity	NPC104216
0.8925	High Similarity	NPC51333
0.8925	High Similarity	NPC252821
0.8925	High Similarity	NPC122005
0.8925	High Similarity	NPC78119
0.8925	High Similarity	NPC216468
0.8925	High Similarity	NPC92730
0.8925	High Similarity	NPC128723
0.8925	High Similarity	NPC132078
0.8913	High Similarity	NPC132271
0.8913	High Similarity	NPC82664
0.8913	High Similarity	NPC292730
0.8913	High Similarity	NPC216520
0.8901	High Similarity	NPC76938
0.8901	High Similarity	NPC152415
0.8901	High Similarity	NPC128062
0.8889	High Similarity	NPC306074
0.8876	High Similarity	NPC70436
0.8851	High Similarity	NPC150837
0.8842	High Similarity	NPC196479
0.883	High Similarity	NPC213730
0.8817	High Similarity	NPC260000
0.8817	High Similarity	NPC152097
0.8804	High Similarity	NPC144682
0.8804	High Similarity	NPC274678
0.8804	High Similarity	NPC32714
0.8791	High Similarity	NPC181709
0.8791	High Similarity	NPC55903
0.8778	High Similarity	NPC300478
0.8737	High Similarity	NPC40258
0.8737	High Similarity	NPC7686
0.8737	High Similarity	NPC91461
0.8723	High Similarity	NPC80027
0.8723	High Similarity	NPC260775
0.8723	High Similarity	NPC280869
0.871	High Similarity	NPC202986
0.8696	High Similarity	NPC245187
0.8696	High Similarity	NPC289769
0.8681	High Similarity	NPC231150
0.866	High Similarity	NPC154899
0.866	High Similarity	NPC138942
0.866	High Similarity	NPC233396
0.8646	High Similarity	NPC168829
0.8632	High Similarity	NPC70677
0.8632	High Similarity	NPC248396
0.8632	High Similarity	NPC129373
0.8632	High Similarity	NPC48730
0.8632	High Similarity	NPC211885
0.8632	High Similarity	NPC166761
0.8632	High Similarity	NPC130756
0.8632	High Similarity	NPC12931
0.8617	High Similarity	NPC32674
0.8617	High Similarity	NPC79241
0.8617	High Similarity	NPC201967
0.8617	High Similarity	NPC107619
0.8617	High Similarity	NPC6597
0.8617	High Similarity	NPC474073
0.8617	High Similarity	NPC109955
0.8617	High Similarity	NPC475078
0.8602	High Similarity	NPC222146
0.8587	High Similarity	NPC271440
0.8571	High Similarity	NPC271274
0.8571	High Similarity	NPC113457
0.8571	High Similarity	NPC135464
0.8571	High Similarity	NPC477814
0.8571	High Similarity	NPC92623
0.8557	High Similarity	NPC8931
0.8557	High Similarity	NPC120693
0.8557	High Similarity	NPC261573
0.8557	High Similarity	NPC288411
0.8556	High Similarity	NPC19680
0.8542	High Similarity	NPC471578
0.8542	High Similarity	NPC101025
0.8542	High Similarity	NPC252105
0.8542	High Similarity	NPC472585
0.8526	High Similarity	NPC245561
0.8526	High Similarity	NPC299762
0.8526	High Similarity	NPC130193
0.8526	High Similarity	NPC33675
0.8511	High Similarity	NPC312132
0.8511	High Similarity	NPC259512
0.8495	Intermediate Similarity	NPC81010
0.8495	Intermediate Similarity	NPC32977
0.8469	Intermediate Similarity	NPC474839
0.8469	Intermediate Similarity	NPC303141
0.8469	Intermediate Similarity	NPC243677
0.8454	Intermediate Similarity	NPC313030
0.8454	Intermediate Similarity	NPC106396
0.8454	Intermediate Similarity	NPC71002
0.8454	Intermediate Similarity	NPC62351
0.8454	Intermediate Similarity	NPC108497
0.8454	Intermediate Similarity	NPC242342
0.8454	Intermediate Similarity	NPC222522
0.8454	Intermediate Similarity	NPC302219
0.8454	Intermediate Similarity	NPC85479
0.8454	Intermediate Similarity	NPC146798
0.8454	Intermediate Similarity	NPC53051
0.8454	Intermediate Similarity	NPC168303
0.8454	Intermediate Similarity	NPC249828
0.8454	Intermediate Similarity	NPC135784
0.8454	Intermediate Similarity	NPC94351
0.8454	Intermediate Similarity	NPC24404
0.8438	Intermediate Similarity	NPC289381
0.8438	Intermediate Similarity	NPC10588
0.8438	Intermediate Similarity	NPC294741
0.8438	Intermediate Similarity	NPC52472
0.8438	Intermediate Similarity	NPC72729
0.8438	Intermediate Similarity	NPC155847
0.8404	Intermediate Similarity	NPC286006
0.8404	Intermediate Similarity	NPC107522
0.84	Intermediate Similarity	NPC31274
0.84	Intermediate Similarity	NPC61885
0.84	Intermediate Similarity	NPC317305
0.84	Intermediate Similarity	NPC63698
0.84	Intermediate Similarity	NPC11554
0.8387	Intermediate Similarity	NPC29373
0.8384	Intermediate Similarity	NPC95178
0.8384	Intermediate Similarity	NPC69332
0.8384	Intermediate Similarity	NPC188677
0.8384	Intermediate Similarity	NPC70843
0.8384	Intermediate Similarity	NPC29989
0.8384	Intermediate Similarity	NPC231705
0.837	Intermediate Similarity	NPC151764
0.837	Intermediate Similarity	NPC47950
0.837	Intermediate Similarity	NPC312304
0.8367	Intermediate Similarity	NPC120719
0.8367	Intermediate Similarity	NPC119860
0.8351	Intermediate Similarity	NPC110764
0.8351	Intermediate Similarity	NPC137415
0.8351	Intermediate Similarity	NPC166313
0.8351	Intermediate Similarity	NPC147310
0.8351	Intermediate Similarity	NPC80800
0.8351	Intermediate Similarity	NPC284011
0.8351	Intermediate Similarity	NPC72947
0.8351	Intermediate Similarity	NPC294186
0.8351	Intermediate Similarity	NPC24407
0.8351	Intermediate Similarity	NPC11280
0.8351	Intermediate Similarity	NPC477685
0.8351	Intermediate Similarity	NPC51015
0.8351	Intermediate Similarity	NPC192032
0.8333	Intermediate Similarity	NPC100870
0.8333	Intermediate Similarity	NPC171843
0.8333	Intermediate Similarity	NPC125732
0.8317	Intermediate Similarity	NPC254833
0.8317	Intermediate Similarity	NPC258056
0.8317	Intermediate Similarity	NPC228343
0.83	Intermediate Similarity	NPC142297
0.83	Intermediate Similarity	NPC228737
0.83	Intermediate Similarity	NPC151477
0.8283	Intermediate Similarity	NPC99557
0.8283	Intermediate Similarity	NPC470393
0.8283	Intermediate Similarity	NPC47284
0.8283	Intermediate Similarity	NPC219286
0.828	Intermediate Similarity	NPC321956

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC280347 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	245
0.1-0.2	1118
0.2-0.3	1306
0.3-0.4	2893
0.4-0.5	1959
0.5-0.6	1087
0.6-0.7	444
0.7-0.8	78
0.8-0.85	9
0.85-0.9	6
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9545	High Similarity	NPD2934	Approved
0.9545	High Similarity	NPD2933	Approved
0.9438	High Similarity	NPD2860	Approved
0.9438	High Similarity	NPD2859	Approved
0.9405	High Similarity	NPD111	Approved
0.9326	High Similarity	NPD1432	Clinical (unspecified phase)
0.913	High Similarity	NPD3020	Approved
0.8804	High Similarity	NPD844	Approved
0.8804	High Similarity	NPD1809	Phase 2
0.8791	High Similarity	NPD845	Approved
0.8737	High Similarity	NPD846	Approved
0.8737	High Similarity	NPD940	Approved
0.8511	High Similarity	NPD288	Approved
0.8367	Intermediate Similarity	NPD9610	Approved
0.8367	Intermediate Similarity	NPD9608	Approved
0.8317	Intermediate Similarity	NPD3022	Approved
0.8317	Intermediate Similarity	NPD3021	Approved
0.8247	Intermediate Similarity	NPD3028	Approved
0.8247	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD9087	Approved
0.8061	Intermediate Similarity	NPD1242	Phase 1
0.802	Intermediate Similarity	NPD1445	Approved
0.802	Intermediate Similarity	NPD1444	Approved
0.8	Intermediate Similarity	NPD2228	Approved
0.8	Intermediate Similarity	NPD2234	Approved
0.8	Intermediate Similarity	NPD2229	Approved
0.7864	Intermediate Similarity	NPD2684	Approved
0.7816	Intermediate Similarity	NPD9294	Approved
0.781	Intermediate Similarity	NPD228	Approved
0.781	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD1792	Phase 2
0.7788	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD4750	Phase 3
0.7727	Intermediate Similarity	NPD9088	Approved
0.7677	Intermediate Similarity	NPD9273	Approved
0.7664	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD5303	Approved
0.7636	Intermediate Similarity	NPD5304	Approved
0.7636	Intermediate Similarity	NPD3091	Approved
0.7596	Intermediate Similarity	NPD2342	Discontinued
0.757	Intermediate Similarity	NPD821	Approved
0.757	Intermediate Similarity	NPD9379	Approved
0.757	Intermediate Similarity	NPD7843	Approved
0.757	Intermediate Similarity	NPD9377	Approved
0.757	Intermediate Similarity	NPD7635	Approved
0.7568	Intermediate Similarity	NPD4093	Discontinued
0.7549	Intermediate Similarity	NPD9500	Approved
0.7545	Intermediate Similarity	NPD16	Approved
0.7545	Intermediate Similarity	NPD856	Approved
0.7523	Intermediate Similarity	NPD255	Approved
0.7523	Intermediate Similarity	NPD6671	Approved
0.7523	Intermediate Similarity	NPD256	Approved
0.75	Intermediate Similarity	NPD4589	Approved
0.75	Intermediate Similarity	NPD3019	Approved
0.75	Intermediate Similarity	NPD4059	Approved
0.75	Intermediate Similarity	NPD968	Approved
0.75	Intermediate Similarity	NPD2932	Approved
0.75	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD5451	Approved
0.7431	Intermediate Similarity	NPD1791	Approved
0.7431	Intermediate Similarity	NPD1793	Approved
0.7429	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD9089	Approved
0.7387	Intermediate Similarity	NPD317	Approved
0.7387	Intermediate Similarity	NPD318	Approved
0.7368	Intermediate Similarity	NPD3092	Approved
0.7364	Intermediate Similarity	NPD7157	Approved
0.7345	Intermediate Similarity	NPD1751	Approved
0.7333	Intermediate Similarity	NPD3134	Approved
0.7321	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD2562	Approved
0.7304	Intermediate Similarity	NPD2561	Approved
0.7297	Intermediate Similarity	NPD9568	Approved
0.7283	Intermediate Similarity	NPD9093	Approved
0.7281	Intermediate Similarity	NPD3421	Phase 3
0.7273	Intermediate Similarity	NPD9614	Approved
0.7273	Intermediate Similarity	NPD9618	Approved
0.7273	Intermediate Similarity	NPD475	Phase 2
0.7264	Intermediate Similarity	NPD290	Approved
0.7257	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD5535	Approved
0.7241	Intermediate Similarity	NPD6582	Phase 2
0.7241	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4659	Approved
0.7241	Intermediate Similarity	NPD6583	Phase 3
0.7222	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD9295	Approved
0.7193	Intermediate Similarity	NPD4626	Approved
0.7193	Intermediate Similarity	NPD3095	Discontinued
0.7193	Intermediate Similarity	NPD2668	Approved
0.7193	Intermediate Similarity	NPD2286	Discontinued
0.7193	Intermediate Similarity	NPD2667	Approved
0.7182	Intermediate Similarity	NPD5283	Phase 1
0.7168	Intermediate Similarity	NPD1548	Phase 1
0.7168	Intermediate Similarity	NPD9545	Approved
0.7158	Intermediate Similarity	NPD9073	Approved
0.713	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD3143	Discontinued
0.713	Intermediate Similarity	NPD3847	Discontinued
0.7119	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD3055	Approved
0.7119	Intermediate Similarity	NPD3094	Phase 2
0.7119	Intermediate Similarity	NPD3053	Approved
0.7119	Intermediate Similarity	NPD4103	Phase 2
0.7117	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4818	Approved
0.7115	Intermediate Similarity	NPD4817	Approved
0.7103	Intermediate Similarity	NPD1358	Approved
0.708	Intermediate Similarity	NPD9616	Approved
0.708	Intermediate Similarity	NPD9613	Approved
0.708	Intermediate Similarity	NPD9615	Approved
0.7069	Intermediate Similarity	NPD422	Phase 1
0.7069	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2195	Approved
0.7059	Intermediate Similarity	NPD7451	Discontinued
0.7059	Intermediate Similarity	NPD6584	Phase 3
0.7059	Intermediate Similarity	NPD2194	Approved
0.7048	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD9381	Approved
0.7043	Intermediate Similarity	NPD9384	Approved
0.7037	Intermediate Similarity	NPD74	Approved
0.7037	Intermediate Similarity	NPD9266	Approved
0.7034	Intermediate Similarity	NPD5311	Approved
0.7034	Intermediate Similarity	NPD5310	Approved
0.7018	Intermediate Similarity	NPD7330	Discontinued
0.7018	Intermediate Similarity	NPD316	Approved
0.7018	Intermediate Similarity	NPD1759	Phase 1
0.7009	Intermediate Similarity	NPD3070	Discontinued
0.7	Intermediate Similarity	NPD5736	Approved
0.7	Intermediate Similarity	NPD3637	Approved
0.7	Intermediate Similarity	NPD3635	Approved
0.7	Intermediate Similarity	NPD3636	Approved
0.6991	Remote Similarity	NPD3596	Phase 2
0.6991	Remote Similarity	NPD9493	Approved
0.6991	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.699	Remote Similarity	NPD9611	Approved
0.699	Remote Similarity	NPD9609	Approved
0.699	Remote Similarity	NPD9612	Approved
0.6975	Remote Similarity	NPD1131	Approved
0.6975	Remote Similarity	NPD1134	Approved
0.6975	Remote Similarity	NPD1129	Approved
0.6975	Remote Similarity	NPD1135	Approved
0.6975	Remote Similarity	NPD1133	Approved
0.6957	Remote Similarity	NPD1357	Approved
0.6952	Remote Similarity	NPD855	Approved
0.6952	Remote Similarity	NPD854	Approved
0.6949	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD3685	Discontinued
0.6949	Remote Similarity	NPD9622	Approved
0.6944	Remote Similarity	NPD9267	Approved
0.6944	Remote Similarity	NPD9264	Approved
0.6944	Remote Similarity	NPD9263	Approved
0.6942	Remote Similarity	NPD2606	Approved
0.6942	Remote Similarity	NPD2605	Approved
0.6942	Remote Similarity	NPD4908	Phase 1
0.6939	Remote Similarity	NPD9094	Approved
0.693	Remote Similarity	NPD1758	Phase 1
0.6923	Remote Similarity	NPD1610	Phase 2
0.6923	Remote Similarity	NPD1535	Discovery
0.6897	Remote Similarity	NPD6516	Phase 2
0.6897	Remote Similarity	NPD5846	Approved
0.6891	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4229	Approved
0.6887	Remote Similarity	NPD4656	Approved
0.6887	Remote Similarity	NPD3680	Approved
0.6887	Remote Similarity	NPD4658	Approved
0.6887	Remote Similarity	NPD3682	Approved
0.6887	Remote Similarity	NPD3683	Approved
0.6887	Remote Similarity	NPD4231	Approved
0.6887	Remote Similarity	NPD3681	Approved
0.6885	Remote Similarity	NPD3136	Phase 2
0.6885	Remote Similarity	NPD5156	Approved
0.6885	Remote Similarity	NPD3027	Phase 3
0.6885	Remote Similarity	NPD5155	Approved
0.6875	Remote Similarity	NPD1241	Discontinued
0.687	Remote Similarity	NPD1894	Discontinued
0.687	Remote Similarity	NPD6580	Approved
0.687	Remote Similarity	NPD6581	Approved
0.6864	Remote Similarity	NPD2232	Approved
0.6864	Remote Similarity	NPD2230	Approved
0.6864	Remote Similarity	NPD1481	Phase 2
0.6864	Remote Similarity	NPD2233	Approved
0.6863	Remote Similarity	NPD9296	Approved
0.686	Remote Similarity	NPD2861	Phase 2
0.6857	Remote Similarity	NPD1616	Discontinued
0.6842	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7636	Approved
0.6838	Remote Similarity	NPD1980	Approved
0.6838	Remote Similarity	NPD3023	Approved
0.6838	Remote Similarity	NPD1981	Approved
0.6838	Remote Similarity	NPD3026	Approved
0.6838	Remote Similarity	NPD1983	Approved
0.6838	Remote Similarity	NPD3496	Discontinued
0.6832	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD9495	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data